In keeping with the film's aura of all-too-gritty authenticity, Leo Fitzpatrick had no professional acting experience when he was cast as one of the leads in Larry Clark's controversial first feature Kids (1995). One of the New York teens who hung out in the same downtown "skater" milieu as Kids screenwriter Harmony Korine, Fitzpatrick was recruited to play Telly, the self-professed "Virgin Surgeon" and unknowing AIDS carrier. With his callow looks, foul mouth, and hardened self-confidence, Fitzpatrick's Telly was the ultimate adolescent nightmare; or, in Clark and Korine's view, simply a sign of the 1990s times. Critics split over whether the unrated Kids was a fiction-verité classic or vile exploitation, but all agreed that the untrained Fitzpatrick had created a memorable brute. Fitzpatrick disappeared from the acting radar until he played a bit part in Clark's next feature Another Day in Paradise (1998); he subsequently guest starred on The Practice in 2000.
By 2001, Fitzpatrick landed roles in more mainstream films as well as art house fare. While he played supporting roles in Rebecca Miller's Sundance Film Festival prizewinner Personal Velocity (2001) and Clark's second troubled teen story Bully (2001), Fitzpatrick also appeared in the short-lived summer comedy Bubble Boy (2001) and the fluffy John Cusack-Kate Beckinsale romance Serendipity (2001). Unlike several other cast members, Fitzpatrick's role survived the editing process for Solondz's Storytelling (2002), which made the festival rounds in 2001 before its early 2002 release. Appearing in the caustic "Fiction" portion, Fitzpatrick made the most of his screen time as a cerebral palsy-afflicted college student whose girlfriend discovers the depths of their writing professor's sadism.